Whiskey Lactone

By. Adrieanna

Compound Name:

• 3-Methyl-4-octanolide or quercus lactone
• trans: 3 - Methyl - 4 - octanolide ; Natural insect repellant
• cis: 3 - Methyl - 4 - octanolide ; most important in flavoring whiskey

Molecular Formula:

C9H16O2

Molar Mass:

156.2221

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Whiskey Lactone

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3D Model:

http://www.acs.org/content/acs/en/molecule-of-the-week/archive/molecule-of-the-week-whiskey-lactone.html

http://www.leffingwell.com/glacton.htm

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Historical Backgrounds/Story of Discovery:

Whiskey lactone:This isomer is an important ingrediant in the aroma of whiskey(where it was first identified by Suomalainen and Nykänen in 1970), and other alcoholic beverages that have been aged in oak barrels. It is extracted from the alcoholic beverage from some precursor substances in oak wood. It can be synthesized from a cyclopentane derivative.



Lactones: A lactone is a cyclic ester. It can be seen as the condensation product of an alcohol group -OH and carboxylic acid group -COOH in the same molecule. Caracterized by a closed ring, two or more carbon atoms, and a single endocyclic oxygen atom.



Whiskey:It is said that the practice of distillation was practiced by the Babylonians in Mesopotamia in the second millennium, with perfumes and aromatics being distilled. Distilling technology passed from the medieval Arabs to the medieval Latins, but none with distilling alcohol. The earliest of distilling alcohol was in Italy for medicinal purposes, like smallpox. Soon distilling alcohol spread, in places like Ireland, Scotland, and soon Europe. The Europeans started to distill "Aqua Vitae" or spirit alcohol. The first confirmed written record of distilling whiskey comes from 1405 Ireland. The first evidence of whiskey production comes from an entry in the Exchequer Rolls for 1494. Whiskey production moved out of a monastic setting and into personal homes and farms. The distillation process was still in its infancy, whiskey was not allowed to age. Back then it tasted raw and brutal compared to today. Now it has evolved into a much smoother drink. In America it was used as currency during the American Revolution, and of course the Whiskey Rebellion that erupted in 1791.

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Chemical Properties:

Boiling Point	Melting Point	Density	Solubility
93-94 Celsius mm Hg (lit.)	>110 Celsius	0.952 g/mL at 25 Celsius (lit.)	Solubility in hexane >50% Solubility in water < 0.1%

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Where is it found and obtained:

• Flavoring found American whiskeys
• Found in all types of oaks
• Has a fierce, strong, and sweet smell
• Can be dissolved in any alcohol proportion
• Type of dissimilitude alcohol beverage; made from fermented grain mash
• Natural Whiskey Lactone; found in wine, rum wine, and sherry

Uses and Importance:

• Mainly used for the preparation of coconut, whiskey, and woody flavored food

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References:

http://www.chemspider.com/Chemical-Structure.56625.html
http://commons.wikimedia.org/wiki/File:%28R,R%29-cis-3-Methyl-4-octanolide.svg
http://en.chembase.cn/substance-170863.html#3d_img
http://webbook.nist.gov/cgi/cbook.cgi?ID=C39638670&Mask=200
http://www.chemblink.com/products/39212-23-2.htm

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Inserting a Chime file

For Windows:

1. Install the MDL Chime plug-in
2. Download a Chime file (.pdb)
3. Upload your file
4. Add Widget, Other HTML
5. Paste in the following code: (be sure to change the "yourfilename.pdb" part to your actual file name)

<embed src="http://cornellbiochem.wikispaces.com/space/showimage/yourfilename.pdb" align="baseline" border="2" width="160" height="160" display3d="ball&amp;stick" options3d="specular" startspin="true" spiny="180" spinz="180" color3d="cpk" />

For Mac:

1. Upload your .pdb or .mol file and add to your page as an attachment.
2. Direct users to save the file and open with iMol.